Carbon tetrabromide → HCID 86679484, compound

HRID 1776526Notes

Reaction equation

HRID 1776526 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=2[N:16]([CH2:21][CH2:22]O)[S:17]([CH3:20])(=[O:19])=[O:18])[C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:2]1.C(Br)(Br)(Br)[Br:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:25][CH2:22][CH2:21][N:16]([C:15]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)[S:17]([CH3:20])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86679483HCID 86679483, compound

Product 1

HCID 86679484HCID 86679484, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(cyclopropylmethoxy)-4-(N-(2-hydroxyethyl)-methylsulfonamido)benzoate (0.690 g, 2.009 mmol) in dry DCM (15 ml), CBr4 (0.866 g, 2.61 mmol) was added, followed by triphenylphosphine (0.685 g, 2.61 mmol), and stirring was continued for 2 hours at RT. The solvent was evaporated, and the residue was purified by flash chromatography on silica gel (eluent: EtOAc/petroleum ether 2/8) to give methyl 4-(N-(2-bromoethyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoate as a colorless oil (0.630 g, 1.551 mmol, 77% yield, MS/ESI+ 405.8, [MH]+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography on silica gel (eluent: EtOAc/petroleum ether 2/8)

Sources & evidence

ORD record
ord-7af446b9640e43de940c636370761bd0
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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